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Write out what is important to you

Building your benefits package is a big milestone in anyone’s freelancing journey. It means you are taking the time to make this career more sustainable and healthy. You should feel proud that you are at this point, and I’m excited to help you through it.‍

In this playbook, I’m going to walk you through the process of building your benefits package. You should think of this as a starting point and not the final time you revisit this. We go into freelancing in part because of the flexibility and freedom, and you should apply that to how you treat your benefits. 

In this playbook, you’ll:‍

  • Design your benefits package around your life priorities

  • Identify where you want to set and enforce boundaries

  • Learn about my “hamster method” theory to preventing burnout

  • Codify the ways you will prevent burnout

  • Make sure you put the P in PTO

  • Prepare for clients overstepping boundaries and have messages to push back

  • Identify and set up your insurance and financial benefits

  • Develop your holistic benefits package

‍Let’s dive in.

What exactly is a freelance benefits package?

You’d never accept a job offer without considering the benefits package. Your salary, healthcare, 401(k), stock options, and PTO are all a huge part of whether that job is right for you. 

‍And yet for freelancers, a benefits package is often seen as an afterthought, if it’s considered at all. I had that experience as a new freelancer. It wasn’t until two years into my freelance career that I realized, as my own boss, I was responsible for my benefits. ‍

I didn’t come up with this entire concept of a freelancer benefits package at that moment, but that’s when I started seeing it as a critical component of any freelancer’s life – not just a nice-to-have. ‍

The first benefit I built in was health care. At the tender age of 26, America’s great healthcare policies booted me off my parents’ insurance. After health care, I decided I deserved at least as much PTO as I had at my old W-2 job. 

Over the years, I refined the idea and built more benefits into it as I earned more and more. For example, in 2020, I added therapy to my benefits package because working during the pandemic eroded my work-life boundaries. 

Then, as my business grew and I had more money sitting around than I used to, I started putting it to work in investment accounts and educational purposes like coaches and classes. Over time, I realized that as my personal needs evolve and my business changed, my benefits package should also evolve to match my needs.

‍I also had to work out how to balance my benefits with my partner’s benefits. As freelancers, we have far more flexibility with our time whereas our partners are often still constrained by typical W-2 time off limitations. I’m very happy to go off on my own, but I know other freelancers who have built their benefits package around their partner’s time off. You get to customize your benefits package to match your needs.

The main idea of a benefits package is to:‍

  • Make sure that we, as freelancers, are living the life we want to live.

  • Shift our mindset away from hustling in the moment and towards a long-term plan. 

  • Encourage forward-thinking, so we can stick to our goals and avoid burnout. 

  • Intentionally design a life that suits your needs and goals. 

Remember, your business is a way to sustain your life, not the other way around. 

In this playbook, we’ll walk through these key components of how to build your benefits package:‍

  • Supporting current and future you

  • Managing your day-to-day work-life balance

  • Investing in healthcare and insurance

  • Preventing burnout

  • Taking vacation and sick leave

  • Continuing education

  • Thinking about retirement

Let’s talk about your life priorities

Ready to get started? Your first exercise is simple but requires some deep thought and honesty: Consider what you want your life to look like, and what you want to prioritize. Your efforts in this exercise will define the decisions you make throughout the playbook.

Open up your workbook and reflect on what your life priorities are. Here are some questions to get the wheels turning, but go as broad as you would like.

How many hours a week do you want to work? Do you want to make a big purchase in the next couple of years, like a car or a house? Do you want to prioritize creative projects, learning, time with friends? Do you want a family? Do you want to grow your family? Do you want to spend more time with your family? What activities or hobbies are you pursuing outside of work, and how much time would you like to spend on them?  

Consider your answers. What themes consistently appear in your dream life?

Write down what you want to prioritize in the next year, five years, and ten years. Keep this document handy, because you can expect to refer back to it!

Here’s an example of what my priority plan looked like at the start of my career:

This is just an exercise – you don’t have to marry your priority plan. Mine certainly changed over time as my skills and needs evolved. As freelancers, too, so much can happen within just a year – a new opportunity or client can open up new doors and ideas for you. This isn’t your true north.

Tip: Struggling to think that far in advance? Look to other freelancers for inspiration. For example, after seeing some of my peers clock off at 1 pm, I decided one of my priorities was to spend less time working. I can’t cut down on hours my first year, but I prioritized that for my five-year plan.


You may be wondering what Step 1 has to do with benefits. Don’t worry, we’ll be jumping into designing your workweek and setting boundaries in Step 2. But you have to decide on your ideal life before you can start building the infrastructure to support it. That’s what this step was about.

What are your three priorities for the next year, five years, and ten years of your career and life?

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